EP0133914B1 - Fein gepulverte polyvalente Metallsalze von 2-Mercaptopyridin-N-oxid, Verfahren zur Herstellung derselben und diese enthaltende antibakterielle Zusammensetzungen - Google Patents
Fein gepulverte polyvalente Metallsalze von 2-Mercaptopyridin-N-oxid, Verfahren zur Herstellung derselben und diese enthaltende antibakterielle Zusammensetzungen Download PDFInfo
- Publication number
- EP0133914B1 EP0133914B1 EP84107658A EP84107658A EP0133914B1 EP 0133914 B1 EP0133914 B1 EP 0133914B1 EP 84107658 A EP84107658 A EP 84107658A EP 84107658 A EP84107658 A EP 84107658A EP 0133914 B1 EP0133914 B1 EP 0133914B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- zinc salt
- size
- particles
- mercaptopyridine
- oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/14—Topical contraceptives and spermacides
Definitions
- This invention relates to finely powdered zinc salts of 2-mercaptopyridine-N-oxide and a method for producing same. It also relates to antibacterial compositions comprising such zinc salts.
- Polyvalent metal salts of 2-mercaptopyridine-N-oxide are known to be effective as antibacterial agents and are widely used not only as ordinary bactericides, but also as dandruff removers being added to shampoo or rinse.
- the polyvalent metals of the salts are, for example, calcium, magnesium, barium, strontium, zinc, cadmium, tin or zirconium, of which zinc is widely used.
- EP-A-70 046 describes the preparation of zinc-2-mercaptopyridine-N-oxide in the form of fine crystals having an average size of 0.5 to 2 pm. This finely divided zinc compound is used in the preparation of anti-dandruff shampoos. Further, US-A-3 723 325 discloses the use of antibacterial zinc salt of 2-mercaptopyridine-N-oxide in particulate form with average particle sizes ranging from 0.2 to about 3 pm in shampoos.
- these polyvalent metal salts e.g. zinc salt has a solubility in water of 15 ppm at 25°C and is thus sparingly soluble in water with a high specific gravity, so that they are sold and supplied in the form of a powder or an aqueous dispersion. Because of the high specific gravity, the metal salts have the disadvantage that even when suspended or dispersed in solvent, they are liable to coagulate, settle and separate.
- a finely divided zinc salt of 2-mercaptopyridine-N-oxide having a size distribution of particles, in which the particles having a size below 0.2 pm are contained in an amount of not less than 50 wt.-%, the particles having a size ranging from 0.5 to 1.0 pm are contained in an amount of not more than 15 wt.-% and the particles having a size exceeding 1.0 pm are contained in an amount of not more than 2 wt.-%, with an average particle size below 0.2 pm. Also, there are provided a method for producing the finely divided zinc salts and antibacterial compositions comprising such salts.
- the finely divided zinc salts according to the invention have a size distribution in which not less than 50 wt% of the particles have a size below 0.2 pm.
- the finely divided zinc salts have such a size distribution of particles comprising not less than 50 wt% of the particles having a size below 0.2 pm, not more than 15 wt% of the particles having a size ranging from 0.5 to 1.0 pm, and not more than 2 wt% of the particles exceeding 1.0 ⁇ .1m, with an average size below 0.2 pm.
- the particles have a size distribution comprising not less than 70 wt% of the particles having a size below 0.2 pm, not more than 10 wt% of the particles having a size ranging from 0.5 to 1 pm and substantially free of particles exceeding 1.0 pm, with an average size below 0.15 um.
- the finely divided zinc salt has a size distribution in which not less than 50 wt% of particles have a size below 0.1 pm.
- a preferable size distribution is such that not less than 50 wt% of the particles have a size below 0.1 micron, not more than 15 wt% of the particles have a size ranging from 0.2 to 0.5 pm and not more than 5 wt% of the particles having a size exceeding 0.5 pm, with an average size below 0.1 ⁇ m.
- the size distribution is such that not less than 70 wt% of the particles have a size below 0.1 pm, not more than 10 wt% of the particles have a size ranging from 0.2 to 0.5 pm, and particles having a size exceeding 0.5 ⁇ m are not substantially contained, with an average size below 0.08 pm.
- the finely divided zinc salts of the invention may be prepared by agitating a dispersion of the salt, as it is or admixed with a salt of (meth)acrylic acid-styrenesulfonic acid copolymer having an average molecular weight of from 10,000 to 1,000,000, along with rigid media having a size below 0.5 mm, thereby finely dividing the salt by the shearing strength of the media into fine particles.
- Starting zinc salts are favorably used in the form of an aqueous dispersion.
- Commercially sold dispersions dispersions obtained by dispersing commercially sold powders of such salts, or suitably prepared dispersions may be used.
- the content of the salt in the dispersion is preferably in the range of from 5 to 70 wt%. In view of the production efficiency, higher concentrations are more preferable. It will be noted that commercially sold dispersants of the salts usually contain 50 wt% of the effective component.
- the salts of (meth)acrylic acid-styrenesulfonic acid copolymer used as the dispersant are water-soluble salts of copolymer of acrylic acid and/or methacrylic acid and styrenesulfonic acid, and may be prepared by a known method.
- the molar ratio of (meth)acrylic acid and styrenesulfonic acid in the copolymer ranges from 1/10 to 10/1, preferably from 1/3 to 7/1.
- the molecular weight is from 10,000 to 1,000,000, preferably from 100,000 to 700,000.
- the molecular weight is important in the practice of the invention. If the molecular weight is smaller than 10,000, the zinc salts may not be finely divided, or once formed particles may be considerably coagulated. On the other hand, when the molecular weight is larger than 1,000,000, it becomes difficult to handle because the high viscosity of the water-soluble copolymer salt itself.
- the salts of the copolymers include salts of sodium, potassium, ammonium, monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine or 2-amino-2-methylpropane-1,3-diol.
- Non-neutralized carboxyl groups may be left to an extent of impeding the performance of the copolymer salts.
- the copolymers may comprise a third component in amounts not impeding the nature thereof.
- the third component include styrene, acrylamide, sulfonic acids such as methacryl- sulfonic acid or viriylsulfonic acid, 2-hydroxyethyl acrylate, various acrylates, various methacrylates, N-methylolacrylamide, and other copolymerizable monomers.
- the water-soluble copolymer salts are generally added in an amount not smaller than 0.1 wt%, preferably from 0.5 to 10 wt%.
- the media have a size below 0.5 mm, preferably from 0.1 to 0.2 mm. Although fine division of the zinc salts is possible using media having a size smaller than 0.1 mm, the mixture of the media and the zinc salts is so high in viscosity that handling becomes difficult.
- the materials for the media are rigid materials such as, for example, Ottawa sand, glass, alumina or zircon, of which glasses are preferred.
- the apparatus in which the zinc salts and the media are agitated for fine division of the salts may be sand mills or sand grinders. Any known types of sand mills and sand grinders including vertical and horizontal types may be used in the practice of the invention. Discs may be of any ordinarily used types.
- the temperature at which fine division is effected is preferably from 5 to 30°C. At temperatures exceeding 30°C, it takes a long time before completion of the fine division, making the fine division difficult.
- the mixing ratio of the media and the dispersion of the zinc salt is from 40/60 to 80/20, preferably from 60/40 to 70/30, on the volume basis.
- the zinc salt is filtered under pressure or centrifugally separated to separate the media and the salt dispersion from each other. If necessary, the media may be washed with water thereby obtaining a finely divided metal salt.
- the thus obtained finely divided zinc salt comprises 50 wt% or more of particles having a size below 0.2 micron, preferably 0.1 micron (the size and its distribution are determined using a centrifugal automatic size distribution measuring instrument CAPA-500 (available from Horiba Seisakusho Co., Ltd.)). Because such fine particles have good dispersability, the dispersion obtained is stable over a long term.
- the finely divided metal salts are more stable and more adsorbable on the hair, skin, bark or building materials and are better in antibacterial effect than known counterparts. Accordingly, such finely divided salts can be utilized not only as dandruff in hair cosmetics, but also as ordinary aqueous bactericides using the salts as a dispersion which has never been used because of the problem of dispersion stability.
- the finely divided zinc salt had, as shown in Table 1 below, a size distribution in which particles having a size below 0.2 um were contained in an amount of 83 wt%.
- the finely divided zinc salt had, as shown in Table 2, a size distribution in which particles having a size below 0.2 pm were contained in an amount of 54 wt%.
- the finely divided zinc salt had, as shown in Table 2, a size distribution in which particles having a size below 0.2 pm were contained in an amount of 88 wt%.
- the finely divided zinc salt had, as shown in Table 2, a size distribution in which particles having a size below 0.2 pm were contained in an amount of 64 wt%.
- the finely divided zinc salt had, as shown in Table 2, a size distribution in which particles having a size below 0.2 pm were contained in an amount of 85 wt%.
- the finely divided zinc salt had, as shown in Table 2, a size distribution in which particles having a size below 0.2 pm were contained in an amount of 83 wt%.
- the temperature in the sand grinder was maintained at 20 to 25°C because the mixture was cooled in the mixing vessel.
- the mixture of the glass beads and the finely divided zinc salt was withdrawn and subjected to a centrifugal separator in which the glass beads and the finely divided salt were separated from each other.
- the separated glass beads were transferred to the mixing vessel for reuse.
- the finely divided zinc salt had, as shown in Table 2, a size distribution in which 88 wt% of the particles had a size below 0.2 pm.
- 35S-labelled zinc salt of 2-mercaptopyridine-N-oxide of the invention was dispersed in 500 ml of an aqueous solution of 1.0% sodium polyoxyethylene(2) lauryl sulfate. In the dispersion was placed 30 mg of a bundle of the hair, followed by immersing for 1 minute while agitating at 100 r.p.m. Thereafter, the hair bundle was rinsed twice with running water for 15 seconds and air-dried, after which 10 mg of the hair was exactly weighed and placed in a 20 ml vial.
- Dispersion stability test each zinc salt was dispersed in water in a concentration of 1 %, which was placed in a test tube and allowed to stand for 10 days. After 10 days, the state of the dispersion was visually judged.
- the finely divided zinc salt had, as shown in Table 5, a size distribution in which 91 wt% of the particles had a size below 0.1 pm.
- the finely divided zinc salt had, as shown in Table 5, a size distribution in which 77 wt% of the particles had a size below 0.1 ⁇ m.
- the finely divided zinc salt had, as shown in Table 5, a size distribution in which 50 wt% of the particles had a size below 0.1 pm.
- the finely divided zinc salt had, as shown in Table 6, a size distribution in which 100 wt% of the particles had a size below 0.1 pm.
- the finely divided zinc salt had, as shown in Table 6, a size distribution in which 100 wt% of the particles had a size below 0.1 ⁇ m.
- the finely divided zinc salt had, as shown in Table 6, a size distribution in which 100 wt% of the particles had a size below 0.1 ⁇ m.
- Zinc salts of 2-mecaptopyridine-N-oxide one being a product of the invention (average size of 0.08 pm) and the other being a commercial product (average size of 0.72 pm), were labelled with 35 S.
- the labelled zinc salts were each dispersed in 500 ml of an aqueous solution of 1% sodium polyoxyethylene(2) laurylsulfate. In the dispersion was placed 30 mg of a hair bundle, followed by immersing for 1 minute under agitation at 100 r.p.m. Subsequently, the hair bundle was rinsed twice each with running water for 15 seconds and air-dried, after which 10 mg of the hair was exactly weighed and placed in a 20 ml of vial.
- the dandruff remover had a remarkable dandruff-removing effect and was stable over 3 months or more at room temperature. In contrast, with the remover using a commercial zinc salt product, the zinc salt was precipitated in 3 days.
- aqueous bactericidal composition of the following formulation using a zinc salt of 2-mercaptopyridine-N-oxide according to the invention was prepared.
- This aqueous bactericide was stable over 1 month or more and exhibited a good bactericidal effect when applied to trees.
- This dandruff remover had a remarkable dandruff-removing effect and was stable over 3 months or more at room temperature.
- the zinc salt was found to settle in 1 day.
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT84107658T ATE35132T1 (de) | 1983-07-06 | 1984-07-02 | Fein gepulverte polyvalente metallsalze von 2mercaptopyridin-n-oxid, verfahren zur herstellung derselben und diese enthaltende antibakterielle zusammensetzungen. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12284583A JPS6016972A (ja) | 1983-07-06 | 1983-07-06 | 微粒子化2−メルカプトピリジン−n−オキシド多価金属塩、その製造方法及びそれを含有する抗菌剤 |
JP122845/83 | 1983-07-06 | ||
JP8269084A JPS60224676A (ja) | 1984-04-24 | 1984-04-24 | 微粒子化2−メルカプトピリジン−n−オキシド多価金属塩、その製造方法及びそれを含有する抗菌性組成物 |
JP82690/84 | 1984-04-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0133914A1 EP0133914A1 (de) | 1985-03-13 |
EP0133914B1 true EP0133914B1 (de) | 1988-06-15 |
Family
ID=26423705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84107658A Expired EP0133914B1 (de) | 1983-07-06 | 1984-07-02 | Fein gepulverte polyvalente Metallsalze von 2-Mercaptopyridin-N-oxid, Verfahren zur Herstellung derselben und diese enthaltende antibakterielle Zusammensetzungen |
Country Status (8)
Country | Link |
---|---|
US (1) | US4670430A (de) |
EP (1) | EP0133914B1 (de) |
KR (1) | KR910007885B1 (de) |
DE (1) | DE3472103D1 (de) |
HK (1) | HK34091A (de) |
MY (1) | MY101170A (de) |
PH (1) | PH22881A (de) |
SG (1) | SG27191G (de) |
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DE3584595D1 (de) * | 1984-08-29 | 1991-12-12 | Kao Corp | Antimikrobische suspensionen und antimikrobische haarbehandlungsmittel. |
CA1264566A (en) * | 1984-09-05 | 1990-01-23 | Tetsuji Iwasaki | Biocidal fine powder, its manufacturing method and a suspension for agricultural use containing the above powder |
US4957908A (en) * | 1990-01-08 | 1990-09-18 | Olin Corporation | Chitosan pyrithione as antimicrobial agent useful in personal care products |
US5015632A (en) * | 1990-01-08 | 1991-05-14 | Olin Corporation | Chitosan pyrithione as an antimicrobial agent useful in personal care products |
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US6017936A (en) * | 1997-03-14 | 2000-01-25 | Arch Chemicals, Inc. | Method for producing particles of pyrithione salts and particles so produced |
US6017562A (en) * | 1997-04-28 | 2000-01-25 | Arch Chemicals, Inc. | Non-spherical and non-platelet crystalline forms of pyrithione salts |
US6242007B1 (en) | 1997-04-28 | 2001-06-05 | Arch Chemicals, Inc. | Non-spherical and non-platelet forms of pyrithione salts and methods of making same |
US6465015B1 (en) | 1998-02-24 | 2002-10-15 | Arch Chemicals, Inc. | Sonic method of enhancing chemical reactions to provide uniform, non-agglomerated particles |
US6682724B2 (en) * | 1999-02-23 | 2004-01-27 | Arch Chemcials, Inc. | Sonic method of enhancing chemical reactions to provide uniform, non-agglomerated particles |
WO2001000021A1 (en) * | 1999-06-25 | 2001-01-04 | Arch Chemicals, Inc. | Pyrithione biocides enhanced by silver, copper, or zinc ions |
US7026308B1 (en) | 1999-06-25 | 2006-04-11 | The Procter & Gamble Company | Topical anti-microbial compositions |
DE19961278A1 (de) * | 1999-12-18 | 2001-06-21 | Cognis Deutschland Gmbh | Verwendung von nanoskaligen Antischuppenwirkstoffen |
US7674785B2 (en) * | 2000-06-22 | 2010-03-09 | The Procter & Gamble Company | Topical anti-microbial compositions |
US8119168B2 (en) * | 2002-04-22 | 2012-02-21 | The Procter & Gamble Company | Personal care compositions comprising a zinc containing material in an aqueous surfactant composition |
AU2003218279A1 (en) * | 2002-04-22 | 2003-11-03 | The Procter & Gamble Company | Use of materials having zinc ionophoric behavior |
US9381148B2 (en) | 2003-03-18 | 2016-07-05 | The Procter & Gamble Company | Composition comprising particulate zinc material with a high relative zinc lability |
US8470305B2 (en) | 2002-06-04 | 2013-06-25 | The Procter & Gamble Company | Shampoo containing a gel network |
US20050202984A1 (en) * | 2003-03-18 | 2005-09-15 | Schwartz James R. | Composition comprising zinc-containing layered material with a high relative zinc lability |
US8349301B2 (en) | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network |
US8367048B2 (en) * | 2002-06-04 | 2013-02-05 | The Procter & Gamble Company | Shampoo containing a gel network |
US8361448B2 (en) * | 2002-06-04 | 2013-01-29 | The Procter & Gamble Company | Shampoo containing a gel network |
US9381382B2 (en) * | 2002-06-04 | 2016-07-05 | The Procter & Gamble Company | Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network |
US8491877B2 (en) * | 2003-03-18 | 2013-07-23 | The Procter & Gamble Company | Composition comprising zinc-containing layered material with a high relative zinc lability |
US8361450B2 (en) | 2002-06-04 | 2013-01-29 | The Procter & Gamble Company | Shampoo containing a gel network and a non-guar galactomannan polymer derivative |
US8349302B2 (en) * | 2002-06-04 | 2013-01-08 | The Procter & Gamble Company | Shampoo containing a gel network and a non-guar galactomannan polymer derivative |
US7481873B2 (en) * | 2002-12-20 | 2009-01-27 | Arch Chemicals, Inc. | Small particle copper pyrithione |
US6821326B2 (en) | 2002-12-20 | 2004-11-23 | Arch Chemicals, Inc. | Small particle copper pyrithione |
US20040213751A1 (en) * | 2003-03-18 | 2004-10-28 | Schwartz James Robert | Augmentation of pyrithione activity or a polyvalent metal salt of pyrithione activity by zinc-containing layered material |
US20040191331A1 (en) * | 2003-03-18 | 2004-09-30 | The Procter & Gamble Company | Composition comprising particulate zinc materials having a defined crystallite size |
BRPI0409100B1 (pt) * | 2003-04-09 | 2014-08-05 | Osmose Inc | Produto de madeira, e, método para conservar um produto de madeira |
US8637089B2 (en) * | 2003-04-09 | 2014-01-28 | Osmose, Inc. | Micronized wood preservative formulations |
US8747908B2 (en) * | 2003-04-09 | 2014-06-10 | Osmose, Inc. | Micronized wood preservative formulations |
MXPA05013850A (es) * | 2003-06-17 | 2006-05-17 | Phibro Tech Inc | Conservador particulado para madera y metodo para producir el mismo. |
US20050252408A1 (en) | 2004-05-17 | 2005-11-17 | Richardson H W | Particulate wood preservative and method for producing same |
EP1799776B1 (de) * | 2004-10-14 | 2013-01-02 | Osmose, Inc. | Mikronisierte holzschutzmittel in organischen trägern |
WO2007133808A2 (en) * | 2006-05-15 | 2007-11-22 | Liquidia Technologies, Inc. | Nano-particles for cosmetic applications |
EP2744339A2 (de) * | 2011-08-15 | 2014-06-25 | The Procter and Gamble Company | Körperpflegezusammensetzungen mit getrocknetem zinkpyrithion |
WO2013025744A2 (en) | 2011-08-15 | 2013-02-21 | The Procter & Gamble Company | Personal care methods |
EP3295931A1 (de) | 2011-10-07 | 2018-03-21 | The Procter & Gamble Company | Shampoozusammensetzung mit einem gelnetzwerk |
WO2016094663A2 (en) | 2014-12-11 | 2016-06-16 | University Of Houston System | Adsorption of fluorinated anesthetics within the pores of molecular crystals |
US10945935B2 (en) | 2016-06-27 | 2021-03-16 | The Procter And Gamble Company | Shampoo composition containing a gel network |
EP3487940B1 (de) | 2016-07-19 | 2021-08-18 | Behr Process Corporation | Antimikrobielle lackzusammensetzung und zugehörige verfahren |
CN112261931B (zh) | 2018-06-05 | 2023-12-08 | 宝洁公司 | 透明清洁组合物 |
EP3894015A1 (de) | 2018-12-14 | 2021-10-20 | The Procter & Gamble Company | Shampoozusammensetzung mit blattförmigen mikrokapseln |
US11896689B2 (en) | 2019-06-28 | 2024-02-13 | The Procter & Gamble Company | Method of making a clear personal care comprising microcapsules |
CN216735268U (zh) | 2020-02-14 | 2022-06-14 | 宝洁公司 | 包装和泵式分配器 |
US11633072B2 (en) | 2021-02-12 | 2023-04-25 | The Procter & Gamble Company | Multi-phase shampoo composition with an aesthetic design |
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US3723325A (en) * | 1967-09-27 | 1973-03-27 | Procter & Gamble | Detergent compositions containing particle deposition enhancing agents |
DE2104017A1 (de) * | 1970-01-28 | 1971-08-05 | E.R. Squibb & Sons Ine , New York, N.Y. (V.St A.) | Bakterizid und fungizid wirkende, 1-Hydroxy 2 pyndinthion-zinn (IV) salz enthaltende Arzneipraparate |
US4323683A (en) * | 1980-02-07 | 1982-04-06 | The Procter & Gamble Company | Process for making pyridinethione salts |
US4345080A (en) * | 1980-02-07 | 1982-08-17 | The Procter & Gamble Company | Pyridinethione salts and hair care compositions |
DE3165895D1 (en) * | 1980-02-07 | 1984-10-18 | Procter & Gamble | Zinc-pyridinethione salts, a process for making thereof and hair care compositions containing them |
ZA814318B (en) * | 1980-07-02 | 1982-07-28 | Hoffmann La Roche | Organo-aluminium compounds |
DE3127863A1 (de) * | 1981-07-15 | 1983-02-03 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur herstellung des zinksalzes von 2-merkaptopyridin-n-oxid in einer leicht filtrierbaren aber gut suspendierbaren form |
-
1984
- 1984-07-02 EP EP84107658A patent/EP0133914B1/de not_active Expired
- 1984-07-02 DE DE8484107658T patent/DE3472103D1/de not_active Expired
- 1984-07-03 US US06/627,479 patent/US4670430A/en not_active Expired - Lifetime
- 1984-07-04 PH PH30920A patent/PH22881A/en unknown
- 1984-07-06 KR KR1019840003915A patent/KR910007885B1/ko not_active IP Right Cessation
-
1987
- 1987-03-18 MY MYPI87000318A patent/MY101170A/en unknown
-
1991
- 1991-04-11 SG SG271/91A patent/SG27191G/en unknown
- 1991-05-02 HK HK340/91A patent/HK34091A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
KR850000963A (ko) | 1985-03-14 |
HK34091A (en) | 1991-05-10 |
US4670430A (en) | 1987-06-02 |
KR910007885B1 (ko) | 1991-10-04 |
DE3472103D1 (en) | 1988-07-21 |
MY101170A (en) | 1991-07-31 |
EP0133914A1 (de) | 1985-03-13 |
SG27191G (en) | 1991-06-21 |
PH22881A (en) | 1989-01-19 |
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